• Ian Gilliam & The FireKings with Carrie’s Soul Food Truck

    We're kicking off the weekend with Ian Gilliam & The FireKings. They'll be treating us all to their incredible "Blues, Rockabilly, Honky Tonk, and Rock & Roll music" live inside the cozy confines of our tropical oasis. Plan on bringing all of your friends and 

  • Lockjaw Classic Rock Band

    It's going to a great Saturday evening with lock returning to our indoor tropical oasis! They'll have us rocking to their awesome sounds covering fan favorites spanning the decades from the 60's through the 80's, and beyond. Saturday, July 11th, from 5 to 8pm. Open 

  • Tara Mills Band

    It's going to be a super cool Sunday Funday with music by the Tara Mills Band. Tara Mills leads the band featuring guitar, banjo, bass, and mandolin. They'll be entertaining all with an original blend of folk, bluegrass, and Americana --- as Tara calls it 

  • Bunch O’Mugs

    Our cup is running over with excitement to announce that Bunch O' Mugs is making their official debut with us here at Glass House Winery & Brewery! This brand new musical blend has been percolating and is ready to be savored! While the blend is 

  • Midnight Buzz Duo

    Get ready for a fantastic Sunday Funday with music by the Midnight Buzz Duo, featuring the talented husband-and-wife team Tracey and Barry Collins. They will be delivering a special acoustic performance filled with classic rock favorites. Grab your favorite GHW&B wine or brew, unwind, and 

  • The Gladstones (no food truck)

    We are super stoked to announce that The Gladstones are returning to our tropical oasis here in Free Union! Bring your friends, grab your favorite GHW&B wine or brew, and get ready to rock out to their great rock 'n' roll and original tunes! Friday, 

  • Charlottesville Blues Revue

    We are beyond excited to welcome the Charlottesville Blues Revue to our slice of Free Union Paradise. This mega-talented lineup features area favorites who have performed on our stage, but never all together at the same time. Come early, grab your favorite GHW&B wine or 

  • John Kelly and Gary Green

    We are in for an incredible musical treat featuring fantastic singer/songwriter John Kelly on guitar and vocals joined by the magnificent harmonica wizard Gary Green. Sunday, July 26th, from 2 to 5pm. Open to all. No cover. For more about these two amazing musicians visit 

  • Don’t Look Up (no food truck)

    Elevate your Friday plans with the fantastic sounds of DON'T LOOK UP! Featuring Andy Burdetsky (bass/vocals), Dave Sherman (guitar/vocals), Rob Martin (guitar/vocals), and Lance Foster (drums/vocals). Don't Look Up will have everyone rocking to their awesome Americana music that's deeply rooted in the Blues! Friday,